1680-44-0Relevant articles and documents
1, 4-Diazabicyclo[2.2.2]octane-sulfonic acid immobilized on magnetic Fe3O4?SiO2 nanoparticles: a novel and recyclable catalyst for the one-pot synthesis of 4-aryl-NH-1, 2, 3-triazoles
Bagheri, Sepideh,Heydari, Akbar,Jadidi Nejad, Masoumeh,Pazoki, Farzane,Yazdani, Elahe
, (2020)
Abstract: In this study, the surface of silica-coated magnetic nanoparticles (Fe3O4?SiO2) were successfully functionalized by an organic ligand of 1, 4-Diazabicyclo[2.2.2]octane (DABCO)-sulfonic acid and used as a highly efficient catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles from the benzyl alcohol derivatives, nitromethane and sodium azide in ethanol. Furthermore, this catalyst could be recovered and reused five times without noticeable loss of activity. Graphic Abstract: Fe3O4?SiO2?TCT-DABCO-SO3H nanoparticles were successfully synthesized and used as a novel, recyclable, efficient and heterogeneous catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles.[Figure not available: see fulltext.]
Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst
Song, Chunlan,Yi, Hong,Dou, Bowen,Li, Yiying,Singh, Atul K.,Lei, Aiwen
, p. 3689 - 3692 (2017)
In this work, a direct C-H activation of thiophenes was presented via an oxidation pathway under visible-light irradiation, in which the thiophene radical cation serves as the key intermediate. Various thiophenes and azoles could be transformed into the corresponding amination products well, and H2O was the only byproduct which is environmentally benign. Our results showed that tert-butyl nitrite (TBN) served as the electron transfer mediator and O2 as the terminal oxidant to regenerate the photocatalyst DDQ and revive the photocatalytic cycle.
Efficient, mild synthesis of N-unsubstituted 1,2,3-triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles
Rodríguez-Florencio, Janeth,Martínez-Otero, Diego,García-Eleno, Marco A.,Cuevas-Ya?ez, Erick
, p. 2189 - 2197 (2018)
A small library of diverse N-unsubstituted 1,2,3-triazoles was prepared from the corresponding 1-sulfonyl-1,2,3-triazoles, which were treated only with MeOH at reflux temperature. This process was carried out in good yields showing high efficiency and goo
Highly Regioselective Radical Transformation of N-Sulfonyl-1,2,3-triazoles in Air
Li, Zi,Wei, Qinghua,Song, Longlong,Han, Wangyujing,Wu, Xiang,Zhao, Yun,Xia, Fei,Liu, Shunying
, p. 6413 - 6417 (2019)
The classic transformations of N-sulfonyl-1,2,3-triazoles were processed via nitrogen anion (hydrolysis, etc.) and carbene intermediates, and no efficient examples via radical intermediates were developed. Here, we reported a catalyst-free radical chain t
SYNTHESIS AND PROPERTIES OF 1,2,3-TRIAZOLES THAT CONTAIN A FERROCENYL RING
Boev, V. I.,Kushnir, V. N.,Shevchuk, M. I.,Dombrovskii, A. V.
, p. 550 - 552 (1980)
Ferrocenesulfonyl azide reacts with a number of aroylmethylenetriphenylphosphinomethylenes in dry methylene chloride to give 1,4,5-trisubstituted 1,2,3-triazoles (61-77percent yields), which are readily converted to 4,5-disubstituted 1,2,3-triazoles and ethyl ferrocenesulfonate when they are refluxed in ethanol.The known triphenylphosphazo ferrocenyl sulfone and ethyl diazoacetate are formed in the case of the reaction of ferrocenesulfonyl azide with carbethoxymethylenetriphenylphosphinomethylene.The structures of the synthesized compounds were proved by the results of elementary analysis and IR, UV, and mass spectroscopy.
4-Aryl- NH -1,2,3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide
Wu, Luyong,Wang, Xianghui,Chen, Yuxue,Huang, Qinglan,Lin, Qiang,Wu, Mingshu
, p. 437 - 441 (2016)
4-Aryl-NH-1,2,3-triazoles are valuable compounds in organic chemistry and pharmaceutical chemistry. In this paper, we describe a novel multicomponent reaction of aldehydes, nitroalkanes, and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles. In this transformation, it was found that both the slow addition of nitroalkane and the presence of NaHSO3/Na2SO3 are advantageous to promote the reaction results. Additionally, a series of aldehydes and nitro compounds were investigated.
Developments in Pd catalysis: Synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides
Barluenga, Jose,Valdes, Carlos,Beltran, Gustavo,Escribano, Maria,Aznar, Fernando
, p. 6893 - 6896 (2006)
Another star for the Palladium: The discovery of reactions promoted by the ubiquitous Pd0 catalysts is still possible. 1H-1,2,3-Triazoles are directly obtained by reaction of alkenyl bromides and sodium azide in the presence of a Pd0-xantphos catalyst (see scheme, xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, dba = trans,trans- dibenzylideneacetone). (Chemical Equation Presented).
Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes
Jin, Tienan,Kamijo, Shin,Yamamoto, Yoshinori
, p. 3789 - 3791 (2004)
The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of CuI catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most pro
Silver-catalyzed three-component reaction: synthesis of N 2-substituted 1,2,3-triazoles via direct benzylic amination
Liu, Zhenhua,Hao, Wenjing,Gao, Wen,Zhu, Guangyu,Li, Xiang,Tong, Lili,Tang, Bo
, p. 1001 - 1006 (2019)
A novel Ag(I)-catalyzed benzylic amination reaction with in situ generation of NH-1,2,3-triazoles for N2-substituted 1,2,3-triazole scaffolds is described. This protocol is achieved with easily accessible substrate, broad functional group, good regioselectivity, thus providing the efficient and practical method to diverse N2-substituted 1,2,3-triazole rings with moderate to good yields.
Cycloaddition of: N -sulfonyl and N -sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles
Prasanth, Thumpati,Chakraborti, Gargi,Mandal, Tirtha,Ravichandiran, Velayutham,Dash, Jyotirmayee
supporting information, p. 911 - 915 (2022/02/02)
The cycloaddition of N-sulfonyl and N-sulfamoyl azides with terminal alkynes generally produces amide derivatives via ketenimine intermediates. We herein delineate a Cu(i) catalyzed method using a prolinamide ligand that selectively generates N-sulfonyl a
Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
Geng, Xiao,Huang, Chun,Wang, Li-Sheng,Wu, An-Xin,Wu, Yan-Dong,Yu, Xiao-Xiao,Zhao, Peng,Zhou, You
supporting information, p. 13664 - 13672 (2021/10/01)
We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved
Palladium-Catalyzed Direct Diarylation of 2-Benzyl-1,2,3-triazole: a Simple Access to 4-Aryl- or 4,5-Diaryl-2-benzyl-1,2,3-triazoles and Phenanthro[9,10-d][1,2,3]triazoles
Doucet, Henri,Roisnel, Thierry,Shi, Xinzhe,Soulé, Jean-Fran?ois,Zhang, Jian
, p. 2375 - 2382 (2021/06/28)
The reactivity of 2-benzyl-1,2,3-triazole in palladium-catalyzed direct arylation was studied. The reaction conditions for the selective synthesis of 2-benzyl-4-aryl-1,2,3-triazoles in moderate to high yields using phosphine-free Pd(OAc)2 catalyst and inexpensive KOAc base have been found. Then, from these 4-aryl-1,2,3-triazoles, the palladium-catalyzed C?H bond functionalization of the C5-position allowed the synthesis of the corresponding 4,5-diarylated 2-benzyl-1,2,3-triazoles. This selective 4,5-diarylation of 2-benzyl-1,2,3-triazole was successfully applied for the straightforward building of the π-extended polycyclic heteroaromatic structures phenanthro[9,10-d][1,2,3]triazoles through Pd-catalyzed C4- and C5-intermolecular arylations followed by Pd-catalyzed C?H intramolecular arylation.